(1R,4aR,5S,8aS)-5-[(3S)-4-carboxy-3-methylbutyl]-1,4a,6-trimethyl-2,3,4,5,8,8a-hexahydronaphthalene-1-carboxylic acid

Details

• Internal ID: c65d4ed1-9073-45fe-bb2b-fe41b12026b3
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: (1R,4aR,5S,8aS)-5-[(3S)-4-carboxy-3-methylbutyl]-1,4a,6-trimethyl-2,3,4,5,8,8a-hexahydronaphthalene-1-carboxylic acid
• SMILES (Canonical): CC1=CCC2C(C1CCC(C)CC(=O)O)(CCCC2(C)C(=O)O)C
• SMILES (Isomeric): CC1=CC[C@H]2[C@@]([C@H]1CC[C@H](C)CC(=O)O)(CCC[C@@]2(C)C(=O)O)C
• InChI: InChI=1S/C20H32O4/c1-13(12-17(21)22)6-8-15-14(2)7-9-16-19(15,3)10-5-11-20(16,4)18(23)24/h7,13,15-16H,5-6,8-12H2,1-4H3,(H,21,22)(H,23,24)/t13-,15-,16-,19+,20+/m0/s1
• InChI Key: LQOQUVKDAZZZJV-LBBLDFNBSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₂O₄
• Molecular Weight: 336.50 g/mol
• Exact Mass: 336.23005950 g/mol
• Topological Polar Surface Area (TPSA): 74.60 Ų
• XlogP: 4.50
• Atomic LogP (AlogP): 4.74
• H-Bond Acceptor: 2
• H-Bond Donor: 2
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9834	98.34%
Caco-2	+	0.6279	62.79%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	+	0.5857	58.57%
Subcellular localzation	Mitochondria	0.7571	75.71%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8066	80.66%
OATP1B3 inhibitior	+	0.7988	79.88%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.6521	65.21%
BSEP inhibitior	+	0.7708	77.08%
P-glycoprotein inhibitior	-	0.7724	77.24%
P-glycoprotein substrate	-	0.7341	73.41%
CYP3A4 substrate	+	0.5863	58.63%
CYP2C9 substrate	-	0.5859	58.59%
CYP2D6 substrate	-	0.8733	87.33%
CYP3A4 inhibition	-	0.7100	71.00%
CYP2C9 inhibition	-	0.9514	95.14%
CYP2C19 inhibition	-	0.9510	95.10%
CYP2D6 inhibition	-	0.9538	95.38%
CYP1A2 inhibition	-	0.9029	90.29%
CYP2C8 inhibition	-	0.8473	84.73%
CYP inhibitory promiscuity	-	0.9078	90.78%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9100	91.00%
Carcinogenicity (trinary)	Non-required	0.7070	70.70%
Eye corrosion	-	0.9906	99.06%
Eye irritation	-	0.8719	87.19%
Skin irritation	-	0.5581	55.81%
Skin corrosion	-	0.9725	97.25%
Ames mutagenesis	-	0.8700	87.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4805	48.05%
Micronuclear	-	0.8100	81.00%
Hepatotoxicity	+	0.5289	52.89%
skin sensitisation	+	0.6581	65.81%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.7632	76.32%
Mitochondrial toxicity	+	0.7500	75.00%
Nephrotoxicity	-	0.5997	59.97%
Acute Oral Toxicity (c)	III	0.6938	69.38%
Estrogen receptor binding	+	0.6447	64.47%
Androgen receptor binding	-	0.5367	53.67%
Thyroid receptor binding	+	0.6239	62.39%
Glucocorticoid receptor binding	+	0.7356	73.56%
Aromatase binding	-	0.5578	55.78%
PPAR gamma	-	0.5000	50.00%
Honey bee toxicity	-	0.9308	93.08%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.7300	73.00%
Fish aquatic toxicity	+	1.0000	100.00%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL221	P23219	Cyclooxygenase-1	93.52%	90.17%
CHEMBL2581	P07339	Cathepsin D	92.77%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.79%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.59%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.34%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.34%	97.25%
CHEMBL3359	P21462	Formyl peptide receptor 1	87.63%	93.56%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	85.37%	90.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.71%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.16%	97.09%
CHEMBL4227	P25090	Lipoxin A4 receptor	82.82%	100.00%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	80.67%	96.47%

Plants that contains it

• Ericameria linearifolia

Cross-Links

• PubChem: 162911548
• LOTUS: LTS0187648
• wikiData: Q105155644